Use of the Anti-Oxidant Butylated Hydroxytoluene in situ for the Synthesis of Readily Oxidized Compounds: Application to the Synthesis of the Moth Pheromone (Z,Z,Z)-3,6,9-Nonadecatriene
Noel W. Davies A , Graham Meredith B , Peter P. Molesworth B and Jason A. Smith B CA Central Science Laboratory, Private Bag 74, University of Tasmania, Hobart TAS 7001, Australia.
B School of Chemistry, Private Bag 75, University of Tasmania, Hobart TAS 7001, Australia.
C Corresponding author. Email: jason.smith@utas.edu.au
Australian Journal of Chemistry 60(11) 848-849 https://doi.org/10.1071/CH07223
Submitted: 27 June 2007 Accepted: 15 August 2007 Published: 1 November 2007
Abstract
The triene (Z,Z,Z)-3,6,9-nonadecatriene was synthesized in three steps from methyl linolenate. The key to the synthesis was the use of the anti-oxidant butylated hydroxytoluene in situ to provide protection of the unstable triene from autoxidation during reaction workup. This simple modification resulted in an increase in the yield from 20 to 85% over three steps.
Acknowledgements
P.P.M. is thankful to the University of Tasmania and the Thomas Crawford Foundation for a postgraduate scholarship.
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